SaaStr

AUGUST 19, 2021

Q: When should a bootstrapped startup hire a (CFO, COO, CMO)? How can a CEO hire those C-level positions for the first time as a CEO and entrepreneur? Here are some rough rules: You want a VP of Everything (Sales, Marketing, Product, Eng) by about $1m-$2m ARR. You probably have to hire them one at a time, a bit slowly.

Sales Hiring 286

Sales Hiring Part-Time VPE VPCs (Virtual Private Cloud) Startup 286

SaaStr

AUGUST 9, 2023

Ok now that some time has gone by I can reflect a bit more thoughtfully here. My top mistakes as a SaaS founder/CEO: Not convincing the very, very, very best VPE I knew to join as our VPE. I had a great CTO, but I also needed a truly great VPE to scale past $10m ARR and deal with all those issues.

Part-Time VPE 246

Part-Time VPE Sales Recruiting CTO Scale 246

SaaStr

JANUARY 19, 2022

While there is no legal definition for CTO or bright line between CTO and VPE, I’d suggest a start-up CTO really only has to do a few things — which are very hard: Assemble a small team (3–9) of very good engineers. That often were never anticipated and aren’t part of the job spec. Dear SaaStr: What Makes a Bad CTO?

CTO Hire 285

CTO Hire Part-Time VPE CTO Engineering 285

SaaStr

MARCH 7, 2021

I thought it would be worth drilling down deeper into each of them, and sharing the learnings and mistakes: 1/ Spending less time fixing things, more time recruiting senior folks to own them. No one spends enough time recruiting as it is, after $1m ARR or so. These are all full-time jobs by $1m ARR.

Part-Time VPE 286

Part-Time VPE Sales Recruiting Sales Hiring Scale 286

SaaStr

JUNE 23, 2020

In SaaS, it is recruiting your VPs and management team : SaaS products mostly don’t sell themselves. You can hack managing and finding 1–3 reps yourself, but after that, you really need a VP of Sales. SaaS products get too complex to hack a product roadmap too long. She can be your CTO forever.

Part-Time VPE 307

Part-Time VPE CTO Hire Fractional VPE Sales Recruiting 307

SaaStr

SEPTEMBER 11, 2021

Lately I’ve been working with 5+ SaaS companies all hiring their first VP of Product. That means often it’s not entirely clear who the first VP of Product should report to. A few general learnings: A VP of Product that Reports to CTO / Engineering Rarely Meets With That Many Customers.

Part-Time VPE 312

Part-Time VPE Outsourcing Services CTO Hire CTO 312

SaaStr

SEPTEMBER 26, 2022

Dear SaaStr: When should a bootstrapped startup hire a (CFO, COO, CMO)? How can a CEO hire those C-level positions for the first time as a CEO and entrepreneur? Here are some rough rules: You want a VP of Everything (Sales, Marketing, Product, Eng) by about $5m ARR, and ideally, Sales and Marketing well before that.

Sales Hiring 277

Sales Hiring Part-Time VPE VPCs (Virtual Private Cloud) Startup 277

SaaStr

OCTOBER 9, 2020

Is usually not really a VP of Sales. I don’t know about you, but I’ve had to recruit a lot of types of folks over the years where my domain knowledge was limited. I’ve had to recruit Ph.Ds. Front-end, mid-end, back-end engineers of all sorts and types. Just pass here, nine times out of ten at least.

Sales Hiring 255

Sales Hiring Part-Time VPE CTO Hire Sales Recruiting 255

SaaStr

JULY 12, 2022

As part of that, we wanted to look back at some of our most iconic content and sessions. One of the first what How to Hire a Great VP of Sales at the New York Enterprise Tech Meet-Up (thank you to John Lehr and Work-Bench for setting this up). Then, we have this community in SaaS — SaaStr. SaaStr is Turning 10!

Sales Hiring 278

Sales Hiring Part-Time VPE VP of Engineering Sales Recruiting 278

SaaStr

DECEMBER 28, 2019

With all that behind you … let me challenge you to 10 SaaS New Year’s Resolutions. Pick a few that work for you: Get That Key VP Hire Done in Q1. Enough with the excuses for not having hired your real VP of Sales, or that VP of Engineering, or whatever. Hire a real recruiter.

Part-Time VPE 321

Part-Time VPE Sales Hiring Scale Sales Recruiting 321

SaaStr

MARCH 1, 2024

In SaaS, once you have even a few million in ARR, the #1 challenge is recruiting top-tier VPs and building a truly top-tier management team: SaaS products mostly don’t sell themselves. You can hack managing and finding 1–3 reps yourself, but after that, you really need a VP of Sales.

Scale 269

Scale Part-Time VPE CTO Hire Fractional VPE 269

SaaStr

MARCH 24, 2021

But I think the biggest, #1, mistake successful first-time entrepreneurs in SaaS make time and time again these days is they micromanage too long. I see this again and again, and in SaaS, it’s a real lost opportunity. Engineering. And if you don’t have real VPs yet — dude.

Part-Time VPE 312

Part-Time VPE Sales Hiring Sales Recruiting Finance 312

SaaStr

APRIL 7, 2021

The top SaaS companies grow faster than ever these days. The first type is the kind of management team hired by second+ time founders. Veterans of the SaaS journey. Often folks they convince to once again be a VP of Eng or VP of Sales. But most of us are first-time founders, or close to it.

Part-Time VPE 284

Part-Time VPE Sales Hiring Sales Recruiting CTO Hire 284

TechEmpower SaaS

AUGUST 7, 2023

Should a startup CTO spend their time programming? Here’s a graphic from Socal CTO that illustrates the roles as they change over time: In its earliest days, a startup’s top need is often to produce a product. Hiring a hands-on lead developer might seem like the right move for an early stage startup. What does the role demand?

CTO Hire 390

CTO Hire New CTO CTO Fractional VPE 390

SaaStr

MAY 3, 2021

And if your team knows how to spend it, correctly — find a way to get them the capital they need to grow even faster than plan. And importantly, you need to spend more time with your existing customers (vs. But even if you’ve hired the world’s best VP of Sales … you can’t opt out of sales entirely.

Part-Time VPE 278

Part-Time VPE Sales Hiring Sales Recruiting Outsourcing Services 278

SaaStr

NOVEMBER 29, 2020

An organization that has come together voluntarily to take on a mission, at least in part. They’ll revolt when you make a senior or mid-level hire that as a group, they simply cannot suffer one day longer. The three times it happened to me: A very senior engineer that we just HAD to have. Something organic.

Part-Time VPE 278

Part-Time VPE Sales Hiring CTO Hire Scale 278

SaaStr

AUGUST 25, 2023

Hundreds of thousands of experts are telling you how to succeed in SaaS. SaaStr Founder and CEO Jason Lemkin shares the 10 worst pieces of SaaS advice, excuses, and mistakes founders make, and what to do instead You have to understand how venture capital works. No one has time to have coffee with all of those folks.

Part-Time VPE 242

Part-Time VPE Scale Sales Hiring CTO Hire 242

SaaStr

SEPTEMBER 10, 2021

And he made an observation to me that I’d been thinking about for a very long time, but didn’t know how to express. And for the most part, these were incredibly stressful times, when I was very underpaid, overworked, and worked to the bone. Not just being part of something great — but, Being Great.

Part-Time VPE 286

Part-Time VPE CTO Hire AWS New CTO 286

SaaStr

MAY 16, 2021

But what they don’t have is a good enough founding team: Sometimes, if the prospective founder isn’t super technical, then the CTO/VPE isn’t really great. But great teams find great markets, so that doesn’t really matter}. At least an acqui-hire. They’ve got a rent-a-CTO. At least a single.

Part-Time VPE 257

Part-Time VPE CTO Hire New CTO CTO 257

SaaStr

FEBRUARY 2, 2021

The hardest phase of SaaS, at least for the founders, is the phase from Initial Traction ($1-$2m in ARR + 80%-100% YoY growth) to the next phase — Initial Scale. Inevitability in SaaS comes around $10m in ARR , plus or minus. That’s the power of compounding SaaS revenue. At least, hire 2 VPs at a time.

Scale 257

Scale Part-Time VPE Sales Hiring Scaling 257

SaaStr

AUGUST 13, 2024

1: Don’t hire a VP (or anyone in the early days) that you aren’t 95% sure is great. Founders between a million and $250M are talking about lowering the bar for hiring because they aren’t sure if the person is great or they’re trying to fill a gap. If you aren’t meeting that many, you aren’t taking hiring seriously.

Sales Hiring 300

Sales Hiring Part-Time VPE Venture Capital Fractional VPE 300

SaaStr

FEBRUARY 13, 2021

A top SaaS VC to me the other day: “Once a SaaS business decelerates, it becomes almost hopeless. The good thing about SaaS is the revenue recurs. I wrote a piece some time ago here, a person favorite, about Our Year of Hell. At least some times. Most SaaS markets aren’t natural monopolies.

Part-Time VPE 278

Part-Time VPE Sales Hiring Scale Business 278

SaaStr

JANUARY 22, 2021

As you try to hire up for your SaaS company, you’re going to be faced with a lot of choices and trade-offs. No hire is the perfect package. But there’s one thing I can tell you in SaaS, at least: Almost Everything Except the Product Itself is Sort of the Same at a Given ACV (Annual Contract Value) Level.

Fractional VPE 269

Fractional VPE Sales Hiring Part-Time VPE Engineering 269

SaaStr

NOVEMBER 12, 2020

you don't know what to do: 1/ Spend more time w/existing customers. 2/ Hire 1 great VP. Those are good times indeed. But there will be times when almost all of just not only struggle … but are just sort of out of ideas. Well, this is SaaS. Spend more time with existing customers.

Part-Time VPE 282

Part-Time VPE Sales Hiring Churn Engineering 282

SaaStr

JULY 30, 2024

Okta’s VP of Engineering, Monica Bajaj, and Senior Director of Platform Product Marketing, Priya Ramamurthi, share Okta’s playbook to PLG, developer experience, and Enterprise ARR. The traditional SaaS model doesn’t always scale, and not every company has all the bells and whistles to fund marketing, sales, and customer success teams.

Underperforming Technical Team 276

Underperforming Technical Team Enterprise Scale Payments 276

SaaStr

MARCH 6, 2024

So Okta is one of our favorite SaaS and Cloud leaders. Founder CEO Todd McKinnon was VP of Engineering at Salesforce and left to start Okta in the depths of the last downturn. Customer Count Up 8% Year-over-Year to 18,950 It’s hard to find net net customers after $1B ARR. Wow, what an engine at $2.5

Fractional VPE 276

Fractional VPE Part-Time VPE Scale SMB 276

SaaStr

JUNE 1, 2021

As part of the run up to 2021 SaaStr Annual in the SF Bay Area Sep 27-29 , we’re taking a look back at some of our favorite classic sessions. (And I’m going to skip by my life story, and how I grew up as a small child in India, and how the dusty streets influenced my take on unit economics, and SaaS subscription models.

Part-Time VPE 283

Part-Time VPE Technical Cofounder CTO Hire New CTO 283

SaaStr

APRIL 4, 2019

As a global technology provider powering thousands of SaaS companies, Google is at the forefront of driving exciting and innovative technologies to market. You’ll also learn how leading SaaS companies are able to scale and thrive in this complex, dynamic environment. Eyal Manor – VP, Engineering @ Google Cloud.

Cloud 171

Cloud Scale Trends Machine Learning 171

BetterCloud

MAY 7, 2021

Prior to joining BetterCloud as our new VP of engineering, she served as a director of engineering at Twilio. We sat down with Brandon to discuss her vision for engineering at BetterCloud, her approach to building teams, and her advice to young female engineers. I’m a big fan of creating innovation time.

Part-Time VPE 52

Part-Time VPE Engineering Innovation Leadership 52

Chart Mogul

DECEMBER 12, 2024

2024 was a big year for SaaS with AI in the spotlight and new pricing models shaking things up. This time last year, 24 SaaS experts predicted big things for 2024. SaaS demand remained conservative, capital didnt aggressively return, and private GPTs failed to gain traction. Next we’ll be hiring it.

Fractional VPE 40

Fractional VPE Software Review SaaS Part-Time VPE 40

SaaStr

JUNE 28, 2020

” In this episode of the SaaStr podcast, Aileen and SaaStr Founder Jason Lemkin take a deep dive on how Aileen finds deals, her tips for a winning pitch, and the state of VC in 2020. 347: Ready to hire your first VP Sales? But I think for a lot of vertical SaaS, they’ll see impacts when the Q2 numbers come out.

Part-Time VPE 187

Part-Time VPE Sales Hiring Payment Methods SaaS Payments 187

SaaStr

JULY 30, 2019

Scott Beechuk, Partner at Norwest Venture Partners, brings together world-class SaaS engineering leaders Claire Hough, Vijay Gill and Weiping Peng for a dynamic conversation on where SaaS technology is headed, how to build top performing engineering teams and what it takes to lead in today’s high-velocity engineering environment.

Engineering 150

Engineering Part-Time VPE Technical Review Fractional VPE 150

SaaStr

OCTOBER 24, 2022

Anyone who says the developer market is not strong is behind the times. The developer-led sales motion is different from a typical SaaS sale where you might sell top-down from a sales-led approach, wherein you’re starting with management, and the execution filters down to the wider org. You’ll need to find developers where they are.

Outsourced Development 207

Outsourced Development Underperforming Technical Team Development Part-Time VPE 207

SaaStr

JULY 8, 2020

We’ll have some time. It sounds minor or technical, but if you want to due diligence on a human being, I get to do it a few 100 times a year. I used it in kind of my breakfast pre warm-up, the crazy times we’re in. From Satya from Homebrew, we just heard that seed’s at an all time high.

Investment 204

Investment Technical Review Part-Time VPE Development Team Review 204

Outseta

MAY 8, 2020

Musing after a decade spent building SaaS start-ups By Geoff Roberts 20 min read. Today I can look back across a full decade that’s been spent building SaaS start-ups. I find that refreshing. Exactly 10 years ago today—May 10, 2010—I slinked through office doors that opened to my first day of work at a “real job.”

Part-Time VPE 102

Part-Time VPE Fractional VPE Sales Hiring Underperforming Technical Team 102

SaaStr

OCTOBER 17, 2019

I actually think I never met any company that have not made a few mistakes about build versus buy and most of the time it’s linked to the long term cost. First of all, I think any good engineer can easily give you 10 good reason to build instead of buy. It’s super easy, like we never find enough arguments to buy.

Scale 164

Scale Scaling CTO Hire Part-Time VPE 164

OpenView Labs

OCTOBER 11, 2019

Pricing is an incredibly important part of any SaaS product’s go-to-market strategy. At Hired, we started out with a transactional model that was—at the time—a super disruptive approach and one of our key differentiators. And—like everything else in the fast-moving SaaS world—pricing is not a once-and-done task.

Sales Hiring 40

Sales Hiring Part-Time VPE CTO Hire Technical Review 40